title: Synthesis and in vitro evaluation of a novel radioligand for αvβ3 integrin receptor imaging: [18F]FPPA-c(RGDfK).
abstract: The development of RGD-based antagonist of αvβ3 integrin receptor has enhanced the interest in PET probes to image this receptor for the early detection of cancer, to monitor the disease progression and the response to therapy. In this work, a novel prosthetic group (N-(4-fluorophenyl)pent-4-ynamide or FPPA) for the (18)F-labeling of an αvβ3 selective RGD-peptide was successfully prepared. [(18)F]FPPA was obtained in three steps with a radiochemical yield of 44% (decay corrected). Conjugation to c(RGDfK(N3)) by the Cu(II) catalyzed Huisgen azido alkyne cycloaddition provided the [(18)F]FPPA-c(RGDfK) with a radiochemical yield of 29% (decay corrected), in an overall synthesis time of 140 min.
authors.affiliation: Cyclotron Unit, University Hospital of Geneva, Rue Gabrielle Perrte-Gentil 4, Geneva 1211, Switzerland; School of Pharmaceutical Sciences, University of Geneva and University of Lausanne, Quai Ernest Ansermet 30, Geneva 1211, Switzerland.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Monaco
authors.forename: Vincent
authors.initials: V
authors.lastname: Zoete
authors.forename: Gian Carlo
authors.initials: GC
authors.lastname: Alghisi
authors.forename: Curzio
authors.initials: C
authors.lastname: Rüegg
authors.forename: Olivier
authors.initials: O
authors.lastname: Michelin
authors.forename: John
authors.initials: J
authors.lastname: Prior
authors.forename: Leonardo
authors.initials: L
authors.lastname: Scapozza
authors.forename: Yann
authors.initials: Y
authors.lastname: Seimbille
mesh_terms: D000577:Amides / Q000737:chemistry*; D045744:Cell Line, Tumor; D057930:Click Chemistry; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D005464:Fluorobenzenes / Q000737:chemistry; D057809:HEK293 Cells; D061307:Human Umbilical Vein Endothelial Cells; D006801:Humans; D039302:Integrin alphaVbeta3 / Q000032:analysis* / Q000737:chemistry; D007553:Isotope Labeling / Q000379:methods; D008958:Models, Molecular; D057054:Molecular Imaging / Q000379:methods; D009842:Oligopeptides / Q000737:chemistry*; D049268:Positron-Emission Tomography / Q000379:methods; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000577:Amides; D005462:Fluorine Radioisotopes; D005464:Fluorobenzenes; D039302:Integrin alphaVbeta3; D009842:Oligopeptides; D019275:Radiopharmaceuticals; C047981:arginyl-glycyl-aspartic acid
keywords: Click chemistry; Positron emission tomography; [(18)F]-labeling; c(RGDfK); αvβ3 Integrin